Tetrahydrofuran → HCID 131724911, compound

HRID 1353777Notes

Reaction equation

HRID 1353777 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14](C#N)[CH:15]=3)[N:10]([CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][O:20]3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[O:25]1[CH:29]=[CH:28][CH:27]=[C:26]1Cl.C([N:33]([CH2:36]C)CC)C.[O:38]1CCC[CH2:39]1>>[C:36]([CH:22]1[CH2:21][O:20][CH:19]([N:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:8]([C:4]3[CH:3]=[C:2]([NH:1][C:39]([C:26]4[O:25][CH:29]=[CH:28][CH:27]=4)=[O:38])[CH:7]=[CH:6][CH:5]=3)=[N:9]2)[CH2:24][CH2:23]1)#[N:33]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 1378562-ChlorofuranHCID 22480146HCID 22480146, compound

Product 1

HCID 131724911HCID 131724911, compound

Procedure

To a solution of 3-(3-aminophenyl)-1-perhydro-2H-pyran-2-yl-1H-indazole-5-carbonitrile (0.300 g, 0.94 mmol) in tetrahydrofuran (10 mL), was added 2-furyl chloride (0.139 mL, 1.41 mmol) and triethyl amine (0.655 mL, 4.7 mmol). After stirring at room temperature overnight, the reaction mixture was concentrated under reduced pressure and the residue was partitioned between ethyl acetate and water. The organic phase was dried under vacuum and the title product was purified by column chromatography (SiO2, 20–30% ethyl acetate in hexanes) (0.370 g, 95%): ES-MS (m/z) 413 [M+H]+.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customthe residue was partitioned between ethyl acetate and water
  3. customThe organic phase was dried under vacuum
  4. customthe title product was purified by column chromatography (SiO2, 20–30% ethyl acetate in hexanes) (0.370 g, 95%)

Sources & evidence

ORD record
ord-729f18fc86ff40f1a17edf4af678f707
Source dataset
uspto-grants-2007_05
Patent number
US07220771B2

Reaction notes

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